Novel fragmentation reaction of correolide

被引：3

作者：

Bao, JM ^{[1
]}

Baker, RK ^{[1
]}

Doss, GA ^{[1
]}

Kayser, F ^{[1
]}

Kotliar, A ^{[1
]}

Miao, SW ^{[1
]}

Parsons, WH ^{[1
]}

Rupprecht, KM ^{[1
]}

机构：

[1] Merck Res Labs, Dept Med Chem, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 11期

关键词：

D O I：

10.1021/ol020053g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Pentacyclic triterpenoid natural product correolide (1) was converted to ketone 2 via ozonolysis. An unusual fragmentation reaction of ketone 2 with LiCl was discovered. This reaction is general among several similar substrates examined and appears to be specific for the correolide-type E-ring structure (ketone). A mechanism involving a retroaldol reaction, a nucleophilic opening of the epoxide, and a subsequent acetoxy elimination reaction was proposed.

引用

收藏

页码：1871 / 1873

页数：3

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